We recently connected with Jack Byron and have shared our conversation below.

Jack , thanks for joining us, excited to have you contributing your stories and insights. Can you take us back in time to the first dollar you earned as a creative – how did it happen? What’s the story?

The first dollar I ever earned for playing music was while I was busking on the streets of downtown Chicago. It was a very surreal experience for me, standing out there, singing and playing from about 12pm-8pm, Monday-Friday, from spring to late fall.

I was in the company of the other street artists as well; magicians, mimes, other musicians, the bronze and silver statue people, and of course the homeless folks in the area. We were all trying to make a buck, just trying to get by.

One of the street magicians had a family too, and he would spend winter in Louisiana performing his show down there, once Chicago started to get too cold.

I would see the same cast of characters on the same corners, on the same days of the week, like clockwork. I found it ironic that it seemed as though there was still the feeling of a 9-5 day, even though the archetype of a street artist has the veneer of irresponsibility.

You see, even though I had decided to go all in and dedicate my life to being an artist, I still had the thorn of practicality twisting into my side, and I had to figure out how to generate some income to prove to myself that a life as an artist could be sustainable for me.

I was new to the Chicago area music scene, had no contacts, and no track record of shows, making it hard to secure shows from venues. So the idea came to me to get my street performers permit, and that’s what I did.

I had a little Roland Street Cube amplifier for my guitar and vocals that could run on 6 double A batteries for about 4-5 hours at a time. I would set up by the Wrigley Building on Michigan Avenue or the Starbucks on South Michigan Avenue. The Wrigley Building has a Walgreens inside of it, which made it easy to get replacement batteries and get a snack when I got hungry. The money from the first hour or two playing would often be spent on my batteries, snacks, and bus and train ticket for the day.

Also, The kind folks at that particular Starbucks on Michigan Avenue would give me free coffee and tea as the weather started getting a bit colder, so I guess they liked what I was playing, and I was grateful to have the warm cup, since once the weather turned cold, the steel on the acoustic guitar really started grinding into my fingers, which could be quite painful at times. Hot Hands became a friend and a. constant companion as well.

Then one day, a girl named Sam who worked at the Potbelly Sandwich Shop at 200 S. Michigan Avenue gave me her contact info. She introduced herself to me while I was busking, and I remember that she had a very radiant and warm smile. She told me that she liked what I was doing and I should consider playing at her Potbelly shop. She was the manager there and she was looking to add another afternoon musician on Wednesdays.

Apart from the passerby’s on the street giving me gifts ranging from food, smiles, frowns, free advice, to penny’s to even a hundred dollar bill on a few occasions, Sam’s offer to me to play as a Potbelly musician was a gesture that changed the course of my entire life. It allowed me to actually receive a check in my bank account for music services rendered, and that gave me the strength and courage to believe that it was truly possible to make a living doing what I love.

After that, I was put in touch with Claire, the booker for all of the Potbelly Shops, and soon enough I was playing 5 days a week at potbelly. Soon after that, I started to get my first paid shows.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I grew up on the south side of the city of Chicago. I always did feel myself to be a bit of an outsider, when I look back on it. I believe that the combination of being raised in foster care and the fact that I was a minority in my neighborhood growing up has contributed to that feeling. My family was very heavy into music though, and their love of music, particularly my dad’s, really had a greatly beneficial impact on me. I can see it in my minds eye, how my dad, would be listening to 97.9 the Loop on the way home, and if a tune like “LA Woman” would be playing, he wouldn’t turn the car off when he parked it. He would listen to the whole song, then turn off the car. That may seem insignificant to most, but to me that suggested a deeper understanding and appreciation of music as an art form. It also showed me the power of a great song, how it can stop someone dead in their tracks, take them into another world, and effect them in the best ways in the core of their being.

My mom was into Elvis and Country Music, Patsy Cline and Toby Keith were some of her favorites, and my dad was into Rock and Motown, and they were both into doo wop groups from the 50’s, The Beatles (the early records) and Mexican music, the latter stemming from my dad’s Hispanic ethnicity. Once my brother in law came around, he turned me on to the blues, which of course turned me on to the guitar like never before. I was 14 at that time.

I got my first guitar and learned my first chord from my brother in law. It was A minor, the opening chord for the Beatles’ tune “Things We Said Today.”

But, It was my grandpa Jack who was really the one who would plant that little seed in the back of my mind, the one that would grow into an obsession with being a serious musician. I would always plunk his out of tune piano when we would visit him and my grandma, and he would always say the same thing to me: “Hey boy, you should play country.”

He was from Alabama and he greatly loved country music; Johnny Cash, George Jones, and Hank Williams to name a few. He never really played guitar, but he messed around with it and knew the opening riff of “I Walk the Line” by Johnny Cash, which he taught me, and has become one of my fondest memories.

My upbringing in foster care was the glue that allowed me to be exposed to so much great music. It has allowed me to view life through a very interesting lens, and that is one important thing that sets me apart from other artists in the field of music.

Being raised in a multi ethnic home has fostered within me a more open minded and tolerant worldview. Being raised along side my African American brother and sister, my Mexican dad, my Caucasian mom, and their own two biological daughters has given me a firsthand view and a real life application of how these larger ideas of different people coexisting together played out on a micro level.

Truth be told, existing in this way is not always easy, but definitely worth the struggles and rewards of experiencing and embracing it.

There was a lot of outside disapproval from strangers as well as even loved ones, but there were also folks who were larger minded and more accepting than that, and that has always given me great hope for the future.

My experiences in foster care (good and bad) coupled with my ability to synthesis the happiness, sadness and grief I’ve experienced in my life and turn that into songs that other people can enjoy and relate to is one thing I am particularly proud of.

It’s what I have dedicated my whole mind and heart to.

It’s not the easiest thing to turn something ugly in your life into something beautiful and useful, but to me, it’s a noble task. Music is the greatest medium to make that happen, and I thank God for that.

I believe that as we work on our getting to know ourselves, and as we grow and heal individually, we in turn heal the world.

My songs are my contribution to the world and my wish is that they can help, encourage, and be relatable to anyone who listens to them. At the very least, I would like them to know that they are not alone in experiencing the struggles and triumphs of life.

What’s the most rewarding aspect of being a creative in your experience?

I would say that for me, the most rewarding aspect of being an artist is when a song of mine reaches down into the depths of someones soul and causes a stir, that moment of genuine human connection between that person and themselves and that person and me.

In a world full of overstimulation and tranquilization of the physical and spiritual senses, the right song can cut through all of the red tape of life and tap into the heart of a person.

As an artist, I can express who I really am without the need of a political party, religion, creed, or any groupthink or peer pressure. Of course, we all have our sympathies, but my self expression comes from inside of me and how I really feel.

I often times feel as though I am contradictory and paradoxical, how I feel today may not be how I feel tomorrow, but that seems to be embedded into the very nature of life, and so because I am alive, I have a contradictory and paradoxical nature as well.

For me, being an artist makes me feel alive and allows me to explore these facets of myself in a meaningful way, and reconcile the apparently contradictory and opposite nature of things.

In my view, the heart is where everything begins and where everything ends, where everything flows into, and where everything flows out of. It is the center of everything, and it is where my songs come from.

Connecting with an audience member in this way, on the heart level, helps me to see that I am not alone in my feelings, and it is my hope that through my songs, whoever hears them will know they are not alone in their feelings, and arguably more importantly, that it’s ok to express insecurities, anxieties, and doubts about yourself and about life.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

A lesson I’ve had to unlearn is that old adage, “Knowledge is Power.” I would like to amend it to “The proper application of constructive knowledge is true power.”

I sometimes talk too much and I think I know everything. I also can be anxious and I tend to overthink, sometimes to a crippling degree. Of course, I know that I don’t actually know everything, but that has really never stopped me from periodically acting that way in conversation, especially the ones that intrigue me most.

Then, one day I had that revelation about myself.

Even if I did know a lot, I was using my so called “knowledge” to make myself look better or feel superior to the person I was conversing with. This false knowledge was actually contributing to my own anxiety and tendency to overthink.

I had knowledge about this economic system and that economic system, this war and that war, this god and that god, this song and that song, this movie and that movie, this time and that time, etcetera, etcetera. This kind knowledge was only puffing up my ego, but it made me feel more powerful perhaps, but in a fleeting kind of way, never sticking around.

It turned out to be a very false power, always needing validation from the subject it was being directed to, always outside of myself, of course. This, to me, suggested a deep seated insecurity within myself, a deep seated fear of not being heard or my thoughts not being valued or validated by the ones I love. This was no doubt the result of my childhood traumas.

I was projecting this fear into my own life and inviting more of it by keeping this fear alive in my day to day conversations by subconsciously trying to appear smarter than whoever I happened to be talking to was.

Until then, I hadn’t prayed for wisdom, I was only interested in knowledge. If I had asked for wisdom, I would have received it and she would have led me to a deeper well of knowledge that would have entrusted me with a true inner power.

Since that revelation, I have been seeking wisdom over more knowledge, and my mind is much clearer since focusing on wisdom over knowledge.

I seek wisdom, and then she leads me to the knowledge that I need in the moment, and that wisdom often times sounds like “love your neighbor as yourself.’

I guess it’s the simple things I tend to forget the most.

But I feel like I am finally starting to ask the right questions and I am trying to keep my focus on the knowledge and power of love, which seems like it could occupy all of the space in my mind from here until eternity.

I’ve discovered that knowledge in and of itself means very little if it isn’t directed toward a more noble and virtuous cause, and can actually turn into a vanity as well as a liability.

Asking the right questions is more important than having all the answers.

Contact Info:

• Website: jackbyron.com
• Instagram: @jackbyronmusic
• Facebook: @jackbyronmusic
• Youtube: @jackbyronmusic

Image Credits
Erik James (JPEG) Jack Loizzo